Sulfuric Acid → 2-(2'-Hydroxy-methylphenyl) benzotriazole

HRID 257651

Reaktionsgleichung

Reaktionsgleichung von HRID 257651
[OH-].[Na+].[O:3]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[N:23]1[N+:27]([O-])=[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]2=[N:24]1.S(=O)(=O)(O)O>C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.O.CO>[OH:3][C:18]1[C:19]([CH3:22])=[CH:20][CH:21]=[CH:16][C:17]=1[N:23]1[N:27]=[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]2=[N:24]1

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

Produkt 1

HCID 135808092-(2'-Hydroxy-methylphenyl) benzotriazoleAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10241FluorenoneKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To the wet product 12 g (~ 0.4 mol) thus obtained, is added methanol (60 ml), water (30 ml), 97% sodium hydroxide (13.0 g) and 9-fluorenone (0.5 g), and glucose (5.5 g) (0.3 mol) is further added to the mixture over an hour while stirring at 50° to 55° C. The mixture is reacted while stirring at 75° C. (boiling point) for 5 hours. As a result, the N-oxide disappears. The reaction liquor is neutralized with 62% sulfuric acid (19.8 g) to pH 8 to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with water and further with methanol. The washed crystal is then dried, thus obtaining 9.4 g of 2-(2'-hydroxy-methylphenyl) benzotriazole having a melting point of 128 to 130° C. at the yield of 92.8%. One can see that the reduction with aromatic ketones takes over 9 hours to complete. This reduction also required the use of two catalysts and a greater amount of total catalysts.

Aufarbeitung

  1. additionis further added to the mixture over an hour
  2. customThe mixture is reacted
  3. stirringwhile stirring at 75° C. (boiling point) for 5 hours
  4. customto precipitate a crystal
  5. customThe precipitated crystal is separated by filtration
  6. washthe separated crystal is fully washed with water and further with methanol
  7. customThe washed crystal is then dried

Quellen und Nachweise

ORD-Eintrag
ord-adf81cdb482147bb8d95ef8e5d349c21
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262541

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